m-Tolylisothiocyanate → Thienopyrimidine deriv. 65

HRID 227626

Reaktionsgleichung

Reaktionsgleichung von HRID 227626
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[S:10][C:9]=2[CH3:18])=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:21]=[C:22]([N:26]=[C:27]=[S:28])[CH:23]=[CH:24][CH:25]=1>CN(C=O)C>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:27]([NH:26][C:22]4[CH:23]=[CH:24][CH:25]=[C:20]([CH3:19])[CH:21]=4)=[S:28])=[CH:7][CH:6]=3)=[C:9]([CH3:18])[S:10][C:11]=2[N:12]=[CH:13][N:14]=1

Komponenten

4

Edukt 2

HCID 69304m-TolylisothiocyanateHCID 65399685-(4-Aminophenyl)-6-methylthieno[2,3-d]pyrimidin-4-amine

Produkt 1

HCID 6539974Thienopyrimidine deriv. 65Ausbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of Example 1E (60 mg, 0.23 mmol) and 3-methylphenyl isothiocyanate in DMF (2 mL) was stirred at room temperature, for 48 hours, quenched with water, and filtered. The filter cake was dried to provide the desired product (75 mg, 80%). MS(ESI(+)) m/e 406 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 9.96 (s, 1H); 9.84 (s, 1H); 8.27 (s, 1H); 7.65 (d, J=8.4 Hz, 2H); 7.35 (d, J=8.4 Hz, 2H); 7.30-7.18 (m, 3H); 6.97 (d, J=6.9 Hz, 1H); 2.30 (s, 6H).

Aufarbeitung

  1. customquenched with water
  2. filtrationfiltered
  3. customThe filter cake was dried

Quellen und Nachweise

ORD-Eintrag
ord-e9e43410ddf145fcad3dadf6b8e5628a
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560552B2

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